When a Series A founder lost a deal and roughly $500,000 in runway because an assistant missed an investor follow-up, we stopped treating matching as a checklist. That incident directly influenced the SigridMatch Framework: a layered process that aligns skills, context, confidentiality, and async workflows before an assistant begins calendar or inbox ownership. Every step that follows is designed to prevent high-cost mismatches and protect executive time.
SigridMatch combines a structured intake, competency assessment, culture-fit scoring, and a staged trial to produce a single output: the assistant profile that minimizes risk and maximizes impact. The framework uses concrete inputs—role responsibilities, stakeholder map, tech stack (Notion, Asana, Slack, Google Workspace, 1Password), and response SLAs—so matching is repeatable and auditable. We treat the match as a deliverable with defined KPIs, not a hiring guess.
Intake is a 45–60 minute session where we map the executive’s week, key stakeholders, and outcome goals: scheduling cadence, inbox triage rules, and stakeholder communication templates. For founders and COOs scaling remote teams under 25 people, we include product release windows, investor schedules, and fundraising milestones so an assistant isn’t only skilled but contextually prepared. This prevents misalignments that cost time and money.
Candidates run task simulations built around the executive’s real work: calendar optimization in Google Calendar, inbox triage with Gmail+SaneBox patterns, and project handoffs in Asana or ClickUp. We score responses on speed, judgment, and security hygiene—do they use 1Password for shared credentials, can they redact sensitive content, do they follow documented escalation rules? This is how we separate general virtual assistant services from a vetted executive assistant who can own confidential workflows.
We evaluate written communication and async-first behaviors because remote collaboration is mostly text. Candidates write a 200–300 word status update in Notion and draft a stakeholder email for a mock board scheduling conflict. Preference goes to EAs who demonstrate clear, concise async updates, proactive agenda design, and a habit of documenting decisions—traits that predict smooth handoffs and continuity during transitions.
We augment human matches with AI-enabled systems to ensure continuity during time off or transitions. Assistants set up AI-assisted inbox triage with templates and an internal RAG (retrieve-and-generate) knowledge base in Notion linked to the executive’s preferences. We require shared SOPs and a documented “handoff folder” so another MySigrid assistant or an AI agent can maintain 80–90% operational parity within 24 hours when coverage is needed.
Match quality is inseparable from security. Our process requires 2FA, enterprise password vaults (1Password), role-based access controls in Google Workspace, and an NDA workflow before any calendar or inbox access. Onboarding templates capture escalation paths and data-retention rules so every assistant match is compliant and auditable—essential when you compare the cost of a bad match to the cost of a full-time replacement.
Every match begins with a 30-day ramp and measurable outcomes: inbox reduction targets, meeting prep turnaround, and stakeholder satisfaction scores. Typical outcomes for matched clients are 10–15 hours reclaimed per week, 70% faster meeting prep, and a 40% lower cost compared with hiring a full-time EA in high-cost markets. If the match doesn’t meet agreed KPIs, we rapidly rematch under the same SLA.
Aisha, founder of an 18-person fintech, needed an EA who could handle investor relations, legal scheduling, and tight data control. Using SigridMatch we paired her with an assistant who scored 95% on our security checklist, aced the Asana-based task simulation, and presented a Notion investor digest template. Within three weeks Aisha reported reclaiming 12 hours a week and reducing investor follow-up latency from 48 hours to under 4 hours—directly protecting deal momentum.
AI speeds onboarding and preserves context but does not make the match. We use OpenAI for draft generation, Zapier for vetted automations, and internal RAG systems to surface historical decisions, but human judgment determines who receives calendar ownership or inbox privileges. The match is human-led and AI-enabled, which yields the reliability executives require when deciding between virtual assistant vs. executive assistant engagement levels.
Our matching process uses concrete artifacts: intake templates in Notion, task simulations in Asana, secure credential vaults in 1Password, and a rematch playbook stored in Notion. We also align on preferred project management tools—Asana, ClickUp, or Linear—during intake so the candidate has real-world familiarity. These artifacts are included with every placement and reduce ramp time to 2–4 weeks.
Founders ask: “How is an EA different from a virtual assistant?” Our process shows the difference: an EA gains ownership of confidential workflows, stakeholder communication, and strategic time management after passing SigridMatch vetting. They aren’t a generic VA; they are a growth multiplier trained on your playbooks and backed by secure tooling and outcome-based KPIs.
Begin with a focused intake call where we collect tech stack, 3-week priorities, and a stakeholder map. We then present a candidate within 7–10 business days, begin a 30-day ramp, and provide onboarding templates and SLAs. To learn specifics about role types and tiered support, see our Executive Assistant page and explore our pricing tiers on Plans & Pricing.
“Match quality is measurable: better matches save time, prevent expensive mistakes, and keep momentum.” — MySigrid Head of Matching
Matching the right executive assistant is a structured operational problem, not a hiring lottery. Our SigridMatch Framework reduces risk with task-driven assessments, security-first onboarding, AI-enabled continuity, and outcome-based guarantees so founders and COOs reclaim time and protect critical milestones. Ready to transform your operations? Book a free 20-minute consultation to discover how MySigrid can help you scale efficiently.